Hydroxyamine hydrochloride → Methyl 4-[(hydroxyimino)methyl]-2-methylbenzoate

HRID 386740Notes

Reaction equation

HRID 386740 reaction equation
[CH:1]([C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1)=O.Cl.[NH2:15][OH:16].C([O-])(=O)C.[Na+]>O1CCCC1.O>[OH:16][N:15]=[CH:1][C:3]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([CH3:13])[CH:4]=1

Participants

6

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 20134203Methyl 4-formyl-2-methylbenzoate

Product 1

HCID 86643375Methyl 4-[(hydroxyimino)methyl]-2-methylbenzoateYield 92.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 4-formyl-2-methylbenzoate (1.3 g) in tetrahydrofuran (50 mL) was added dropwise to a solution of hydroxylamine hydrochloride (1.0 g), sodium acetate (1.2 g) in tetrahydrofuran (50 mL) and water (50 mL) under ice cooling, and after finishing the dropwise addition, the mixture was stirred for one hour at room temperature. The reaction mixture was diluted with water and then extracted with ethyl acetate, and the organic layer was dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain a crude product of methyl 4-[(hydroxyimino)methyl]-2-methylbenzoate (1.3 g).

Workup

  1. additionthe dropwise addition
  2. extractionextracted with ethyl acetate
  3. dry with materialthe organic layer was dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-dff59267f489481e86563c37196d46f2
Source dataset
uspto-grants-2013_02
Patent number
US08372867B2

Reaction notes

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